Thionyl Chloride → HCID 68410091, compound

HRID 1511610Notes

Reaction equation

HRID 1511610 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:15][C:16]([OH:18])=O)[CH2:7][CH2:8][C:9]1[O:10][C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:5])[CH3:2].S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:15][C:16](=[O:18])[C:13]2[CH:12]=[C:11]([CH3:14])[O:10][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 68410994HCID 68410994, compound

Product 1

HCID 68410091HCID 68410091, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

[Ethoxycarbonyl[2-(5-methylfuran-2-yl)ethyl]amino]-acetic acid (0.17 g) prepared in the step 5 was dissolved in 3.5 mL of methylene chloride, then 0.12 g of thionyl chloride and 1 drop of DMF were added thereto and the mixture was heated to reflux for 2 hours. After the reaction solution was cooled, it was diluted with 5 mL of methylene chloride, then 0.18 g of aluminum chloride was added thereto and the mixture was heated to reflux again for 30 minutes. After the reaction solution was cooled, it was poured over 50 mL of ice water, the organic layer was separated, washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 0.07 g of the objective compound as yellow liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter the reaction solution was cooled
  4. temperaturethe mixture was heated
  5. temperatureto reflux again for 30 minutes
  6. temperatureAfter the reaction solution was cooled
  7. customthe organic layer was separated
  8. washwashed with water
  9. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2c8c2fbc9b2d45c09d11cb22cdbd5511
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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